CA2264556A1 - N-[aminoiminomethyl ou aminomethyl)phenyl]propylamides substitues - Google Patents
N-[aminoiminomethyl ou aminomethyl)phenyl]propylamides substituesInfo
- Publication number
- CA2264556A1 CA2264556A1 CA002264556A CA2264556A CA2264556A1 CA 2264556 A1 CA2264556 A1 CA 2264556A1 CA 002264556 A CA002264556 A CA 002264556A CA 2264556 A CA2264556 A CA 2264556A CA 2264556 A1 CA2264556 A1 CA 2264556A1
- Authority
- CA
- Canada
- Prior art keywords
- pharmaceutically acceptable
- solvate
- compound according
- prodrug
- acceptable salt
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims 9
- -1 aminoiminomethyl Chemical group 0.000 title 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 64
- 108010074860 Factor Xa Proteins 0.000 claims abstract 8
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 2
- 150000003839 salts Chemical class 0.000 claims 57
- 239000012453 solvate Substances 0.000 claims 57
- 239000000651 prodrug Substances 0.000 claims 56
- 229940002612 prodrug Drugs 0.000 claims 56
- 229910052739 hydrogen Inorganic materials 0.000 claims 21
- 239000001257 hydrogen Substances 0.000 claims 21
- 125000000217 alkyl group Chemical group 0.000 claims 19
- 150000002431 hydrogen Chemical class 0.000 claims 12
- 125000001072 heteroaryl group Chemical group 0.000 claims 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 230000002401 inhibitory effect Effects 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 125000004367 cycloalkylaryl group Chemical group 0.000 claims 3
- 125000005215 cycloalkylheteroaryl group Chemical group 0.000 claims 3
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 125000002252 acyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 125000003435 aroyl group Chemical group 0.000 claims 2
- 125000004350 aryl cycloalkyl group Chemical group 0.000 claims 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 2
- 125000005349 heteroarylcycloalkyl group Chemical group 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- GQOIZDFIEBHLKG-UHFFFAOYSA-N 4-tert-butyl-N-[3-(5-carbamimidoyl-2-hydroxyphenyl)propyl]benzamide 2,2,2-trifluoroacetic acid Chemical compound FC(C(=O)O)(F)F.C(C)(C)(C)C1=CC=C(C(=O)NCCCC2=C(C=CC(=C2)C(N)=N)O)C=C1 GQOIZDFIEBHLKG-UHFFFAOYSA-N 0.000 claims 1
- HQULGJDHOPDURG-UHFFFAOYSA-N 5-pyridin-2-ylthiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=CC=N1 HQULGJDHOPDURG-UHFFFAOYSA-N 0.000 claims 1
- NAEPPQRSKXFIMY-UHFFFAOYSA-N FC(C(=O)O)(F)F.C(N)(=N)C=1C=CC(=C(C1)CCCNC(=O)C=1SC2=C(C1)C=CC=C2Cl)O Chemical compound FC(C(=O)O)(F)F.C(N)(=N)C=1C=CC(=C(C1)CCCNC(=O)C=1SC2=C(C1)C=CC=C2Cl)O NAEPPQRSKXFIMY-UHFFFAOYSA-N 0.000 claims 1
- YWXSPXWOLXFCBP-UHFFFAOYSA-N FC(C(=O)O)(F)F.FC(C(=O)O)(F)F.C(N)(=N)C=1C=CC(=C(C1)CCCC1=C(C(=O)N)C=CC(=C1)C=1NC=NC1)O Chemical compound FC(C(=O)O)(F)F.FC(C(=O)O)(F)F.C(N)(=N)C=1C=CC(=C(C1)CCCC1=C(C(=O)N)C=CC(=C1)C=1NC=NC1)O YWXSPXWOLXFCBP-UHFFFAOYSA-N 0.000 claims 1
- HRCFDHWCIKKQGE-UHFFFAOYSA-N N-[3-(5-carbamimidoyl-2-hydroxyphenyl)propyl]-4-(1H-imidazol-2-yl)benzamide 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.NC(=N)c1ccc(O)c(CCCNC(=O)c2ccc(cc2)-c2ncc[nH]2)c1 HRCFDHWCIKKQGE-UHFFFAOYSA-N 0.000 claims 1
- JPMKNKCZMNMCRG-UHFFFAOYSA-N N-[3-(5-carbamimidoyl-2-hydroxyphenyl)propyl]-4-(6-methoxypyridin-3-yl)benzamide 2,2,2-trifluoroacetic acid Chemical compound FC(C(=O)O)(F)F.C(N)(=N)C=1C=CC(=C(C1)CCCNC(C1=CC=C(C=C1)C=1C=NC(=CC1)OC)=O)O JPMKNKCZMNMCRG-UHFFFAOYSA-N 0.000 claims 1
- UCMFFTYQVYPZPM-UHFFFAOYSA-N N-[3-(5-carbamimidoyl-2-hydroxyphenyl)propyl]-4-phenylbenzamide 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.NC(=N)c1ccc(O)c(CCCNC(=O)c2ccc(cc2)-c2ccccc2)c1 UCMFFTYQVYPZPM-UHFFFAOYSA-N 0.000 claims 1
- IUGURGKONYSWDW-UHFFFAOYSA-N N-[3-(5-carbamimidoyl-2-hydroxyphenyl)propyl]-4-piperidin-4-ylbenzamide 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.NC(=N)c1ccc(O)c(CCCNC(=O)c2ccc(cc2)C2CCNCC2)c1 IUGURGKONYSWDW-UHFFFAOYSA-N 0.000 claims 1
- JPIONSXLJKFEHX-UHFFFAOYSA-N N-[3-(5-carbamimidoyl-2-hydroxyphenyl)propyl]-4-pyridazin-4-ylbenzamide 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.NC(=N)c1ccc(O)c(CCCNC(=O)c2ccc(cc2)-c2ccnnc2)c1 JPIONSXLJKFEHX-UHFFFAOYSA-N 0.000 claims 1
- 108090000190 Thrombin Proteins 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- JGUUDVREZDLARD-CQWFHMBZSA-N methyl (2r,3r)-2-[(3-carbamimidoylphenyl)methyl]-3-[[4-(6-oxo-1h-pyridin-3-yl)benzoyl]amino]butanoate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C([C@@H](C(=O)OC)[C@@H](C)NC(=O)C=1C=CC(=CC=1)C1=CNC(=O)C=C1)C1=CC=CC(C(N)=N)=C1 JGUUDVREZDLARD-CQWFHMBZSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 229960004072 thrombin Drugs 0.000 claims 1
- 230000001668 ameliorated effect Effects 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
- C07D207/327—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
- C07C255/60—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton at least one of the singly-bound nitrogen atoms being acylated
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
- C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
- C07C257/18—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to carbon atoms of six-membered aromatic rings
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/12—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines
- C07C259/18—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines having carbon atoms of hydroxamidine groups bound to carbon atoms of six-membered aromatic rings
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
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- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/40—Acylated substituent nitrogen atom
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/55—Acids; Esters
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/56—Amides
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/57—Nitriles
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- C07C2601/14—The ring being saturated
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- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/08—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing three- or four-membered rings
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Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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US08/884,405 | 1997-06-27 | ||
US08/884,405 US6080767A (en) | 1996-01-02 | 1997-06-27 | Substituted n-[(aminoiminomethyl or aminomethyl)phenyl]propyl amides |
PCT/US1998/013550 WO1999000356A1 (fr) | 1997-06-27 | 1998-06-26 | N-[aminoiminomethyl ou aminomethyl)phenyl]propylamides substitues |
Publications (2)
Publication Number | Publication Date |
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CA2264556A1 true CA2264556A1 (fr) | 1999-01-07 |
CA2264556C CA2264556C (fr) | 2009-12-01 |
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Application Number | Title | Priority Date | Filing Date |
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CA002264556A Expired - Lifetime CA2264556C (fr) | 1997-06-27 | 1998-06-26 | N-[aminoiminomethyl ou aminomethyl)phenyl]propylamides substitues |
Country Status (28)
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US (1) | US6080767A (fr) |
EP (1) | EP0931060B1 (fr) |
JP (1) | JP4107687B2 (fr) |
KR (1) | KR100567148B1 (fr) |
CN (1) | CN1221529C (fr) |
AP (1) | AP1061A (fr) |
AT (1) | ATE449759T1 (fr) |
AU (1) | AU741173B2 (fr) |
BG (1) | BG64867B1 (fr) |
BR (1) | BR9806060B1 (fr) |
CA (1) | CA2264556C (fr) |
CZ (1) | CZ299399B6 (fr) |
DE (1) | DE69841300D1 (fr) |
DK (1) | DK0931060T3 (fr) |
EA (1) | EA002358B1 (fr) |
ES (1) | ES2335825T3 (fr) |
HK (1) | HK1022685A1 (fr) |
HU (1) | HU228982B1 (fr) |
IL (1) | IL128653A (fr) |
NO (1) | NO314758B1 (fr) |
OA (1) | OA10981A (fr) |
PL (1) | PL191115B1 (fr) |
PT (1) | PT931060E (fr) |
SI (1) | SI0931060T1 (fr) |
SK (1) | SK286615B6 (fr) |
UA (1) | UA66346C2 (fr) |
WO (1) | WO1999000356A1 (fr) |
ZA (1) | ZA985664B (fr) |
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JP2003522733A (ja) * | 1999-02-11 | 2003-07-29 | コア セラピューティクス,インコーポレイティド | Xa因子の阻害剤としてのアルケニルおよびアルキニル化合物 |
DE10012732A1 (de) | 2000-03-18 | 2001-09-20 | Aventis Behring Gmbh | Thrombin-Zubereitungen und Verfahren zu ihrer Herstellung |
SE0001803D0 (sv) | 2000-05-16 | 2000-05-16 | Astrazeneca Ab | New compounds i |
GB0108903D0 (en) * | 2000-10-05 | 2001-05-30 | Aventis Pharm Prod Inc | Novel crystalline forms of a factor Xa inhibitor |
US6982251B2 (en) * | 2000-12-20 | 2006-01-03 | Schering Corporation | Substituted 2-azetidinones useful as hypocholesterolemic agents |
US20020183519A1 (en) * | 2001-03-13 | 2002-12-05 | Herbert Nar | Antithrombotic carboxylic acid amides |
GB0124941D0 (en) * | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
GB0124938D0 (en) * | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
GB0124931D0 (en) * | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
GB0124939D0 (en) * | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
GB0124934D0 (en) * | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
GB0124936D0 (en) * | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
GB0124933D0 (en) * | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
BRPI0307351B8 (pt) * | 2002-02-12 | 2021-05-25 | Smithkline Beecham Corp | composto, composição farmacêutica, uso de um composto, e, processo para preparar um composto |
GB0217757D0 (en) | 2002-07-31 | 2002-09-11 | Glaxo Group Ltd | Novel compounds |
EP1394159A1 (fr) * | 2002-08-13 | 2004-03-03 | Warner-Lambert Company LLC | Nouveaux dérivés de thiophène, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent |
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GB0230162D0 (en) * | 2002-12-24 | 2003-02-05 | Metris Therapeutics Ltd | Compounds useful in inhibiting angiogenesis |
WO2004081002A1 (fr) | 2003-03-07 | 2004-09-23 | Schering Corporation | Composes d'azetidinone substitues, leurs formulations et utilisations en vue du traitement de l'hypercholesterolemie |
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CA2517573C (fr) * | 2003-03-07 | 2011-12-06 | Schering Corporation | Composes d'azetidinone substitues, formulations et utilisations de ceux-ci pour traiter l'hypercholesterolemie |
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GB0402143D0 (en) * | 2004-01-30 | 2004-03-03 | Smithkline Beecham Corp | Novel compounds |
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EP1864980A4 (fr) | 2005-03-30 | 2010-08-18 | Eisai R&D Man Co Ltd | Agent antifongique contenant un dérivé de pyridine |
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PL2736888T3 (pl) | 2011-07-26 | 2016-04-29 | Sanofi Sa | Pochodne kwasu 3-heteroaroiloamino-propionowego i ich zastosowanie jako środków farmaceutycznych |
JP6043290B2 (ja) | 2011-09-22 | 2016-12-14 | 武田薬品工業株式会社 | 縮合複素環化合物 |
CA2998375A1 (fr) | 2015-09-17 | 2017-03-23 | Marvin J. Miller | Composes heterocycliques contenant de la benzylamine et compositions utiles contre une infection mycobacterienne |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
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US5424334A (en) * | 1991-12-19 | 1995-06-13 | G. D. Searle & Co. | Peptide mimetic compounds useful as platelet aggregation inhibitors |
US5612353A (en) * | 1995-06-07 | 1997-03-18 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Substituted (sulfinic acid, sulfonic acid, sulfonylamino or sulfinylamino) N-[(aminoiminomethyl)phenylalkyl]-azaheterocyclylamide compounds |
RO117913B1 (ro) * | 1996-01-02 | 2002-09-30 | Aventis Pharmaceuticals Inc. | Derivaţi de n-[(amino-(imino)metil)fenil]propil amide substituite, compoziţie farmaceutică care îi conţine şi metodă de tratament |
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1997
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1998
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- 1998-06-26 DE DE69841300T patent/DE69841300D1/de not_active Expired - Lifetime
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- 1998-06-26 CN CNB988010844A patent/CN1221529C/zh not_active Expired - Lifetime
- 1998-06-26 SI SI9830924T patent/SI0931060T1/sl unknown
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- 1998-06-26 KR KR1019997001592A patent/KR100567148B1/ko not_active IP Right Cessation
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- 1998-06-26 WO PCT/US1998/013550 patent/WO1999000356A1/fr active IP Right Grant
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- 1998-06-26 AU AU81771/98A patent/AU741173B2/en not_active Expired
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1999
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